3,5-diphenyl-valeric acid methyl ester | 64516-63-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3,5-diphenyl-valeric acid methyl ester
• 英文别名: 3,5-Diphenyl-valeriansaeure-methylester；Methyl 3,5-diphenylpentanoate
• CAS: 64516-63-8
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: ZMMMLJNKIULDKI-UHFFFAOYSA-N

物化性质

• 沸点：
  203-204 °C(Press: 13 Torr)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-diphenyl-valeric acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (S)-3,5-diphenyl-1-pentanol 、 (R)-(-)-3,5-diphenylpentan-1-ol
  参考文献：
  名称：

  铜-N-杂环卡宾配合物催化烷基硼烷的对映选择性共轭加成

  摘要：

  首次实现了烷基硼化合物的催化对映选择性共轭加成。烷基硼烷与咪唑-2-基α,β-不饱和酮之间的反应在Cu（I）催化剂体系的影响下以高对映选择性进行，该催化剂体系由CuCl原位制备，CuCl是一种新的手性咪唑盐作为N-杂环的前体卡宾配体和PhOK。烷基硼烷广泛通过烯烃硼氢化反应获得。烷基硼烷和 α,β-不饱和酮可耐受多种官能团。

  DOI：

  10.1021/ja304481a
• 作为产物：
  描述：

  methyl (3R,4S)-4-(1-methylimidazol-2-yl)sulfanyl-3,5-diphenylpentanoate 在 nickel boride 作用下， 以 乙醇 为溶剂， 以87%的产率得到3,5-diphenyl-valeric acid methyl ester
  参考文献：
  名称：

  Casey; Gairns; Walker, Synlett, 2000, # 12, p. 1725 - 1728

  摘要：

  DOI：

文献信息

• Conjugate Addition of RMgX–3MeLi to α,β-Unsaturated Amides and α,β-Unsaturated Carboxylic Acids
  作者：Mikiko Kikuchi、Satomi Niikura、Nao Chiba、Nahoko Terauchi、Morio Asaoka

  DOI：10.1246/cl.2007.736

  日期：2007.6.5

  In the presence of 3 equivalents of MeLi, various Grignard reagents reacted with secondary α,β-unsaturated amides and α,β-unsaturated carboxylic acids to give the corresponding Michael adducts in g...

  在 3 当量的 MeLi 存在下，各种格氏试剂与仲 α,β-不饱和酰胺和 α,β-不饱和羧酸反应，得到相应的迈克尔加合物。
• Acyl radicals: intermolecular and intramolecular alkene addition reactions
  作者：Dale L. Boger、Robert J. Mathvink

  DOI：10.1021/jo00031a021

  日期：1992.2

  A full study of the use of phenyl selenoesters as precursors to acyl radicals and their subsequent participation in intermolecular and intramolecular alkene addition reactions is detailed. Primary alkyl-, vinyl-, and aryl-substituted acyl radicals generated by Bu3SnH treatment of the corresponding phenyl selenoesters participate cleanly in intermolecular addition reactions with alkenes bearing electron-withdrawing or radical-stabilizing substituents at rates that exceed those of the potentially competitive decarbonylation or reduction. Similarly, their intramolecular addition to activated or unactivated alkenes proceeds without significant competitive reduction or decarbonylation and at rates generally greater-than-or-equal-to 1 x 10(6) s-1 with some occurring at rates greater-than-or-equal-to 3 x 10(7) s-1. Consistent with their behavior in intermolecular addition reactions, the 5-exo-trig cyclizations of secondary and tertiary alkyl-substituted acyl radicals to an unactivated olefin acceptor may be accompanied by varying degrees of decarbonylation, even under low-temperature free-radical reaction conditions. Studies are presented which suggest that the intramolecular additions of acyl radicals to alkenes under the conditions detailed herein may be regarded as irreversible, kinetically controlled processes which exhibit regioselectivity that is predictable based on well-established empirical rules set forth for the analogous free-radical cyclization reactions of alkyl radicals.
• Phenyl selenoesters as effective precursors of acyl radicals for use in intermolecular alkene addition reactions
  作者：Dale L. Boger、R. J. Mathvink

  DOI：10.1021/jo00269a001

  日期：1989.4
• Gravel,D. et al., Canadian Journal of Chemistry, 1977, vol. 55, p. 2373 - 2384
  作者：Gravel,D. et al.

  DOI：——

  日期：——
• Zur Kenntnis der Cyclopentan-1, 3-dione. 1. Mitteilung
  作者：A. Maeder

  DOI：10.1002/hlca.19460290118

  日期：——